US4173638A - N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof - Google Patents
N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof Download PDFInfo
- Publication number
- US4173638A US4173638A US05/844,174 US84417477A US4173638A US 4173638 A US4173638 A US 4173638A US 84417477 A US84417477 A US 84417477A US 4173638 A US4173638 A US 4173638A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- urea
- oxy
- chlorobenzoyl
- dichloropyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
Definitions
- the present invention relates to novel N-benzoyl N'-pyridyloxy phenyl ureas and the process for producing the same and the insecticidal composition containing the same.
- N-benzoyl N'-phenyl ureas disclosed in U.S. Pat. No. 3,748,356 have such insecticidal properties.
- N-benzoyl N'-pyridyloxyphenyl ureas according to the present invention have a substantially better action than the above described known compounds.
- novel compounds of the present invention are N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR2## wherein X 1 represents a halogen atom; X 2 represents hydrogen or halogen atom; X 3 and X 4 respectively represent hydrogen or chlorine atom; X 5 represents hydrogen or halogen atom; and X 6 represents a halogen atom or nitro or trifluoromethyl group.
- Suitable compounds having the formula (I) include:
- N-benzoyl N'-pyridyloxy phenyl ureas having the formula (I) are produced by reacting a compound having the formula ##STR3## wherein X 1 represents a halogen atom; X 2 represents hydrogen or halogen atom; R 1 represents amino or isocyanate group with a compound having the formula ##STR4## wherein X 3 and X 4 are the same and different and respectively represent hydrogen or chlorine atom; X 5 represents hydrogen or halogen atom; X 6 represents halogen atom or nitro or trifluoromethyl group; and R 2 represents an amino or isocyanate group and R 2 is amino group in the case that R 1 is isocyanate group, R 2 is isocyanate group in the case that R 1 is amino group.
- the compounds having the formula (I) can be produced by the following processes (1) and (2).
- the reaction is preferably carried out in the presence of a solvent.
- Suitable solvents include benzene, toluene, xylene, pyridine etc.
- the reaction temperature is usually in a range of 20° to 120° C. and the reaction time is usually in a range of 0.5 to 24 hours.
- the reaction is preferably carried out at the temperature from 50° C. to a refluxing temperature for 1 to 5 hours.
- a solution prepared by dissolving 2.9 g of 3-chloro-4-(3,5-dichloro-pyridyl-2-oxy) aniline in 50 ml of toluene was heated at 80° C.
- a solution prepared by dissolving 1.8 g of 2-chlorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the former solution under stirring it and the reaction was carried out for 1 hour.
- Example 2 In accordance with the process of Example 1, except using 2.5 g of 4-(3,5-dichloropyridyl-2-oxy) aniline instead of 3-chloro-4-(3,5-dichloropyridyl-2-oxy) aniline and using 2.4 g of 2,6-dichlorobenzoyl isocyanate instead of 2-chlorobenzoyl isocyanate and reacting at 30° C. for 8 hours instead of 80° C. for 1 hour, the process was repeated to obtain 3.8 g of N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea (m.p. 228° to 230° C.).
- the compounds of the present invention impart excellent selective insecticidal effect as clearly understood from the following experiments.
- the compounds of the present invention impart the delayed effect that the compounds effect to molting (ecdysis) and metamorphosis of specific insects which orally take the compound with feeds or water whereby the death of the specific insects is caused.
- the compounds of the present invention impart remarkable insecticidal effect to larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, for example, larvae of the following insects:
- the compounds of the present invention do not substantially impart insecticidal effect to adults and are ineffective to natural enemies as predatory insects and impart low toxicity to animals.
- compositions such as dust, wettable powder, emulsifiable concentrate, invert emulsion, oil solution, aerosol preparation, etc. with adjuvants as the cases of agricultural compositions.
- the compositions can be applied with or without diluting them in suitable concentrations.
- Suitable adjuvants include powdery carriers such as talc, kaolin, bentonite, diatomaceous earth, silicon dioxide, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile, and alcohol; emulsifiers dispersing agents spreaders etc.
- the concentration of the active ingredient in the selective insecticidal composition is usually 5 to 80 wt.% in the case of the oily concentrate; and 0.5 to 30 wt.% in the case of dust; 5 to 60 wt.% in the case of wettable powder.
- the selective insecticides of the present invention are effective for inhibiting various injurious insects and they are usually applied at a concentration of the active ingredients of 5 to 10,000 ppm preferably 20 to 2,000 ppm.
- the active ingredients were respectively dispersed in water to prepare dispersions having specified concentrations. Leaves of cabbage were dipped into the dispersions for about 10 seconds and taken out and dried under passing air.
- Young branches of persimmon tree cut in a length of 15 cm from the top were respectively dipped into the aqueous dispersions of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea at various concentrations for 10 seconds, and they were dried and put into wide mouth bottles and larvae of gypsy moth in 2nd or 3rd instar were fed into them.
- the bottles were covered with gauze and kept in a constant temperature at 28° C. with lightening. After 7 days and 15 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates and the abnormal rates were calculated. The results are shown in Table 4.
- N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea was used to prepare the aqueous dispersions at specified concentrations. The effects of the dispersions to various insects were tested. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
- the components were uniformly blended to dissolve the ingredient to prepare an emulsifiable concentrate.
- the mixture was pulverized to uniformly mix them to prepare dust.
- the components were pulverized to uniformly mix them to prepare a wettable powder.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; and X6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds.
The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.
Description
1. Field of the Invention
The present invention relates to novel N-benzoyl N'-pyridyloxy phenyl ureas and the process for producing the same and the insecticidal composition containing the same.
2. Description of the Prior Arts
Almost of the conventional insecticides impart neurotoxicity and contact toxicity to all kinds of insects.
And, it has been required to find selective insecticidal compounds without toxicity to useful insects, N-benzoyl N'-phenyl ureas disclosed in U.S. Pat. No. 3,748,356 have such insecticidal properties.
The N-benzoyl N'-pyridyloxyphenyl ureas according to the present invention have a substantially better action than the above described known compounds.
It is an object of the present invention to provide novel N-benzoyl N'-pyridyloxy phenyl ureas.
It is another object of the present invention to provide a process for producing N-benzoyl N'-pyridyloxy phenyl ureas.
It is the other objects of the present invention to provide selective insecticidal compositions which are remarkably effective to certain injurious insects without affecting useful insects in remarkably low toxicity to animals.
The novel compounds of the present invention are N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR2## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; and X6 represents a halogen atom or nitro or trifluoromethyl group.
Suitable compounds having the formula (I) include:
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-bromopyridyl-2-oxy) phenyl]urea m.p. 196° to 199° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-nitropyridyl-2-oxy) phenyl]urea m.p. 209° to 212° C.
N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy) phenyl]urea m.p. 185° to 188° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dibromopyridyl-2-oxy) phenyl]urea m.p. 223° to 224° C.
N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 216° to 218° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 225° to 228° C.
N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 221° to 223° C.
N-(2-chlorobenzoyl)N'-[4-(5-bromopyridyl-2-oxy) phenyl]urea m.p. 179° to 180° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 198° to 200° C.
N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 147° to 148° C.
N-(2-chlorobenzoyl)N'-[4-(5-trifluoromethylpyridyl-2-oxy) phenyl]urea
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-trifluoromethylpyridyl-2-oxy) phenyl]urea
N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 228° to 230° C.
N-(2,6-dichlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 214° to 216° C.
N-(2,6-dichlorobenzoyl)N'-[3,5-dichloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 273° to 275° C.
N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 184° to 185° C.
N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 230° to 231° C.
N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 210° to 212° C.
The N-benzoyl N'-pyridyloxy phenyl ureas having the formula (I) are produced by reacting a compound having the formula ##STR3## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; R1 represents amino or isocyanate group with a compound having the formula ##STR4## wherein X3 and X4 are the same and different and respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; X6 represents halogen atom or nitro or trifluoromethyl group; and R2 represents an amino or isocyanate group and R2 is amino group in the case that R1 is isocyanate group, R2 is isocyanate group in the case that R1 is amino group.
More particularly, the compounds having the formula (I) can be produced by the following processes (1) and (2).
(1) The reaction of benzoyl isocyanate having the formula ##STR5## with pyridyloxy aniline having the formula ##STR6## (wherein X1, X2, X3, X4, X5 and X6 are defined above)
(2) The reaction of benzamide having the formula ##STR7## with pyridyloxy phenyl isocyanate having the formula ##STR8## (wherein X1, X2, X3, X4, X5, and X6 are defined above).
The reaction is preferably carried out in the presence of a solvent. Suitable solvents include benzene, toluene, xylene, pyridine etc.
The reaction temperature is usually in a range of 20° to 120° C. and the reaction time is usually in a range of 0.5 to 24 hours. The reaction is preferably carried out at the temperature from 50° C. to a refluxing temperature for 1 to 5 hours.
Certain examples of preparations of the compounds of the present invention will be described.
A solution prepared by dissolving 2.9 g of 3-chloro-4-(3,5-dichloro-pyridyl-2-oxy) aniline in 50 ml of toluene was heated at 80° C. A solution prepared by dissolving 1.8 g of 2-chlorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the former solution under stirring it and the reaction was carried out for 1 hour. After the reaction, the reaction mixture was cooled and the precipitate was filtered and washed with toluene and then with petroleum ether and dried to obtain 3.2 g of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea (m.p. 225° to 228° C.).
In accordance with the process of Example 1, except using 2.5 g of 4-(3,5-dichloropyridyl-2-oxy) aniline instead of 3-chloro-4-(3,5-dichloropyridyl-2-oxy) aniline and using 2.4 g of 2,6-dichlorobenzoyl isocyanate instead of 2-chlorobenzoyl isocyanate and reacting at 30° C. for 8 hours instead of 80° C. for 1 hour, the process was repeated to obtain 3.8 g of N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea (m.p. 228° to 230° C.).
The compounds of the present invention impart excellent selective insecticidal effect as clearly understood from the following experiments.
Most of the conventional insecticides impart quick effect and neurotoxicity and contact toxicity. However, the compounds of the present invention impart the delayed effect that the compounds effect to molting (ecdysis) and metamorphosis of specific insects which orally take the compound with feeds or water whereby the death of the specific insects is caused.
The compounds of the present invention impart remarkable insecticidal effect to larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, for example, larvae of the following insects:
diamondback moth (Plutella xylostella), common white (Pieris rapae crucivora), cabbage armyworm (Mamesta brassicae), cabbage looper (Plusia nigrisigma), tobacco cutworm (Prodenia litura), smoller citrus dog (Papilio xuthus), small blackfish cochlid (Seopelodes contracta), fall webworm (Hyphantria cunea), gypsy moth (Lymantria dispar), rice stem borer (Chilo suppressalis), bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), bollweevil (Anthonomus grandis), confused flour beetle (Tribolium confusum), colorado potato beetle (Leptinotarsa decemlineata), sawfly (Neurotoma irdescens), Culex mosquito (Culex pipiens pallens).
The compounds of the present invention do not substantially impart insecticidal effect to adults and are ineffective to natural enemies as predatory insects and impart low toxicity to animals.
When the compounds are used as active ingredients of the insecticidal composition, it is possible to prepare various forms of the compositions such as dust, wettable powder, emulsifiable concentrate, invert emulsion, oil solution, aerosol preparation, etc. with adjuvants as the cases of agricultural compositions. The compositions can be applied with or without diluting them in suitable concentrations.
Suitable adjuvants include powdery carriers such as talc, kaolin, bentonite, diatomaceous earth, silicon dioxide, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile, and alcohol; emulsifiers dispersing agents spreaders etc.
The concentration of the active ingredient in the selective insecticidal composition is usually 5 to 80 wt.% in the case of the oily concentrate; and 0.5 to 30 wt.% in the case of dust; 5 to 60 wt.% in the case of wettable powder.
It is also possible to combine with the other agricultural ingredients such as the other insecticides, miticides, plant growth regulators. Sometimes synergetic effects are found.
The selective insecticides of the present invention are effective for inhibiting various injurious insects and they are usually applied at a concentration of the active ingredients of 5 to 10,000 ppm preferably 20 to 2,000 ppm.
The active ingredients were respectively dispersed in water to prepare dispersions having specified concentrations. Leaves of cabbage were dipped into the dispersions for about 10 seconds and taken out and dried under passing air.
A piece of moistened filter paper was put on each Petri dish (diameter 9 cm) and the dried leaves of cabbage were put on the filter paper and larvae of diamondback moth in 2nd or 3rd instar were fed on them and the Petri dishes were covered and kept in constant temperature at 28° C. with lightening. After 8 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the following equation: ##EQU1##
Table 1 ______________________________________ Mortality Rate (%) (concen- tration) 200 100 No. Active ingredient ppm ppm ______________________________________ 1 N-(2-chlorobenzoyl)N'-[3-chloro-4(5-bromo- pyridyl-2-oxy)phenyl]urea 100 100 2 N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-nitro- pyridyl-2-oxy)phenyl]urea 100 100 3 N-(2-chlorobenzoyl)N'-[4-(3,5-dibromo- pyridyl-2-oxy)phenyl]urea 100 100 4 N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5- dibromopyridyl-2-oxy)phenyl]urea 100 100 5 N-(2-chlorobenzoyl)N'-[4-(3,5-dichloro- pyridyl-2-oxy)phenyl]urea 100 100 6 N-(2-chlorobenzoyl)N'-[3-chloro-4- (3,5-dichloropyridyl-2-oxy)phenyl]urea 100 100 7 N-(2,6-dichlorobenzoyl)N-[4-(3,5- dichloropyridyl-2-oxy)phenyl]urea 100 100 8 N-(2,6-dichlorobenzoyl)N'-[3-chloro- 4-(3,5-dichloropyridyl-2-oxy)phenyl]urea 100 100 9 N-(2-chlorobenzoyl)N'-[3,5-dichloro-4- (3,5-dichloropyridyl-2-oxy)phenyl]urea 100 80 10 N-(2,6-dichlorobenzoyl)N'-[3,5-dichloro- 4-(3,5-dichloropyridyl-2-oxy)phenyl]urea 80 60 11 N-(2,6-difluorobenzoyl)N'-[4-(3,5- dichloropyridyl-2-oxy)phenyl]urea 12 100 12 N-(2,6-difluorobenzoyl)N'-[3-chloro-4- (3,5-dichloropyridyl-2-oxy)phenyl]urea 100 100 13 N-(2-chlorobenzoyl)N'-[4-(5-bromo- pyridyl-2-oxy)phenyl]urea 100 100 14 N-(2-chlorobenzoyl)N'-[3-chloro-4- (5-chloropyridyl-2-oxy)phenyl]urea 100 100 15 N-(2-chlorobenzoyl)N'-[3,5-dichloro-4- (5-chloropyridyl-2-oxy)phenyl]urea 100 60 16 N-(2-chlorobenzoyl)N'-[4-(5-trifluoro- methylpyridyl-2-oxy)phenyl]urea 100 80 17 N-(2,6-difluorobenzoyl)N'-[3-chloro-4- (5-chloropyridyl-2-oxy)phenyl]urea 100 100 ______________________________________
On radish young seedlings grown in unglazed pots, adults of diamondback moth were fed and kept for 24 hours to blow ova. One day later, aqueous dispersions of the active ingredients (500 ppm) were respectively sprayed on the young seedlings to fall drops of the dispersion and dried and kept in glass greenhouse. After 10 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the equation ##EQU2##
The results are shown in Table 2.
Table 2 ______________________________________ Mortality rate NO. Active ingredient (%) ______________________________________ 1 N-(2-chlorobenzoyl)N'-[3-chloro-4- (5-nitropyridyl-2-oxy)phenyl]urea 80 2 N-(2-chlorobenzoyl)N'-[3-chloro-4- (3,5-dibromopyridyl-2-oxy)phenyl]urea 100 3 N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5- dichloropyridyl-2-oxy)phenyl]urea 100 ______________________________________
About 20 cc of germinated rice seeds were put into cups (diameter: 9 cm, height: 3 cm) to grow them. When they grew to seedlings having a height of 1 to 2 cm, the aqueous dispersions at specified concentrations were respectively sprayed at a ratio of 2 cc per 1 cup and dried, and larvae of rice stem borer (just hatched) were fed and the cups were covered. After 10 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the equation of Experiment 1. The results are shown in Table 3.
Table 3 ______________________________________ Mortality rate (%) (concentration) No. Active ingredient 200 ppm 100 ppm ______________________________________ 1 N-(2-chlorobenzoyl)N'-[3-chloro-4- (5-bromopyridyl-2-oxy) phenyl] urea 100 100 2 N-(2-chlorobenzoyl)N'-[3-chloro-4- (5-nitropyridyl-2-oxy) phenyl] urea 100 100 3 N-(2-chlorobenzoyl)N'-[3-chloro-4- (3,5-dibromopyridyl)-2-oxy) phenyl] urea 100 100 4 N-(2-chlorobenzoyl)N'-[3-chloro-4- (3,5-dichloropyridyl-2-oxy) phenyl] urea 100 100 ______________________________________
Young branches of persimmon tree cut in a length of 15 cm from the top, were respectively dipped into the aqueous dispersions of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea at various concentrations for 10 seconds, and they were dried and put into wide mouth bottles and larvae of gypsy moth in 2nd or 3rd instar were fed into them. The bottles were covered with gauze and kept in a constant temperature at 28° C. with lightening. After 7 days and 15 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates and the abnormal rates were calculated. The results are shown in Table 4.
Table 4 ______________________________________ Mortality rate (%) (concentration) Observation 400 ppm 200 ppm 100 ppm ______________________________________ After 7 days 100 90 (10)* 40 (30)* After 15 days 100 100 90 (10)* ______________________________________ *abnormal rate
N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea was used to prepare the aqueous dispersions at specified concentrations. The effects of the dispersions to various insects were tested. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
The results are shown in Table 5.
Table 5 ______________________________________ Concent- ration Mortality Insects Treatment (ppm) rate ______________________________________ cabbage armyworm: cabbage leaf 2nd instar larvae dipping 50 100 (Lepidoptera) confused flour beetle: wheat flour 2nd larval instar larvae blending 200 100 (Coleoptera) 1 sp. of sawfly cherry branch 3rd instar larvae spraying 250 100 (Hymenoptera) ______________________________________
200 ml of the aqueous dispersions at specified concentrations were respectively placed in glass containers with a capacity of 450 cc. 20 larvae of third instar of the mosquito (Culex pipiens pallens) were placed in each container and the containers were hold at 26°-28° C. with lightening. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
The results are shown in Table 6.
Table 6 ______________________________________ Mortality rate (%) No. Active ingredient 0.1 ppm 0.01 ppm ______________________________________ 1 N-(2-chlorobenzoyl)N'-[4-(3,5- dibromopyridyl-2-oxy)phenyl] urea 100 100 2 N-(2,6-difluorobenzoyl)N'-[4-(3,5- dichloropyridy-2-oxy)phenyl] urea 100 100 3 N-(2-chlorobenzoyl)N'-[4-(5-bromo- pyridyl)-2-oxy)phenyl] urea 100 100 ______________________________________
______________________________________ (a) N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl- 2-oxy)phenyl]urea 20 wt. parts (b) Dimethyl sulfoxide 70 wt. parts (c) Polyoxyethylenealkylphenyl ether 10 wt. parts ______________________________________
The components were uniformly blended to dissolve the ingredient to prepare an emulsifiable concentrate.
______________________________________ (a) N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl] urea 5 wt. parts (b) Talc 92 wt. parts (c) Sodium naphthalene sulfonate formaldehyde condensate 3 wt. parts ______________________________________
The mixture was pulverized to uniformly mix them to prepare dust.
______________________________________ (a) N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy phenyl]urea 50 wt. parts (b) Jeeklite (fine divided clay) 45 wt. parts (d) Sodium ligninsulfonate 5 wt. parts ______________________________________
The components were pulverized to uniformly mix them to prepare a wettable powder.
Claims (17)
1. N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR9## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; X6 represents a halogen atom or nitro or trifluoromethyl group.
2. N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 which has the formula ##STR10## wherein X7 represents hydrogen or chlorine atom and X8 represents hydrogen or halogen atom; X9 represents a halogen atom.
3. N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea.
4. N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
5. N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
6. N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy)phenyl]urea.
7. N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 which has the formula: ##STR11## wherein X7, X8 and X9 are defined in claim 2.
8. N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
9. N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
10. An insecticidal composition which comprises insecticidally effective amount N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) according to claim 1 in admixture with a suitable carrier or adjuvant therefor.
11. An insecticidal composition according to claim 10 which comprises 0.5 to 80 wt. parts of N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) and 20 to 99.5 wt. parts of an agricultural adjuvant.
12. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea.
13. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
14. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-[chlorobenzoyl)N'-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
15. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy)phenyl]urea.
16. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
17. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/899,461 US4173637A (en) | 1976-10-29 | 1978-04-24 | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP51130903A JPS5840946B2 (en) | 1976-10-29 | 1976-10-29 | N-benzoyl-N'-pyridyloxyphenylurea compounds, methods for producing them, and insecticides containing them |
JP51/130903 | 1976-10-29 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/899,461 Continuation-In-Part US4173637A (en) | 1976-10-29 | 1978-04-24 | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
US4173638A true US4173638A (en) | 1979-11-06 |
Family
ID=15045407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/844,174 Expired - Lifetime US4173638A (en) | 1976-10-29 | 1977-10-21 | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof |
Country Status (14)
Country | Link |
---|---|
US (1) | US4173638A (en) |
JP (1) | JPS5840946B2 (en) |
AR (1) | AR217087A1 (en) |
BE (1) | BE891094Q (en) |
BR (1) | BR7707099A (en) |
DE (1) | DE2748636C2 (en) |
FR (1) | FR2369266A1 (en) |
GB (1) | GB1540351A (en) |
GE (1) | GEP19960347B (en) |
IT (1) | IT1109489B (en) |
KE (1) | KE3184A (en) |
MY (1) | MY8400075A (en) |
SU (1) | SU738491A3 (en) |
UA (1) | UA6347A1 (en) |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4223033A (en) * | 1979-08-24 | 1980-09-16 | Zoecon Corporation | Substituted pyridine methyl esters of naphthyl acids |
EP0040179A2 (en) * | 1980-05-14 | 1981-11-18 | Ciba-Geigy Ag | Phenylbenzoyl urea |
US4310530A (en) * | 1979-09-07 | 1982-01-12 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N-pyridyloxy phenyl urea |
US4321388A (en) * | 1979-09-11 | 1982-03-23 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N'-pyridyloxy phenyl urea |
FR2492822A1 (en) * | 1980-10-24 | 1982-04-30 | Nissan Chemical Ind Ltd | HETEROCYCLIC UREA COMPOUNDS CONTAINING ETHER OR THIOETHER BINDING, PROCESS FOR THEIR PREPARATION AND INSECTICIDE COMPOSITION CONTAINING SAME |
US4431667A (en) * | 1981-12-04 | 1984-02-14 | The Upjohn Company | Imino ethers useful for controlling insect and arachnoid pests |
US4540578A (en) * | 1982-12-30 | 1985-09-10 | Union Carbide Corporation | Pesticidal phenoxypyridyl benzoyl ureas |
US4577028A (en) * | 1981-10-20 | 1986-03-18 | Ciba-Geigy Corporation | 5-Haloalkyl-pyridines |
US4602109A (en) * | 1982-12-30 | 1986-07-22 | Union Carbide Corporation | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation |
US4659724A (en) * | 1982-12-30 | 1987-04-21 | Union Carbide Corporation | Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties |
US4677127A (en) * | 1981-11-10 | 1987-06-30 | Ciba-Geigy Corporation | Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use |
US4861799A (en) * | 1986-10-03 | 1989-08-29 | Ishihara Sangyo Kaisha Ltd. | Benzoylurea compounds and pesticides containing them |
US4973589A (en) * | 1986-08-06 | 1990-11-27 | Ciba-Geigy Corporation | Method of preventing the reinfestation of dogs and cats by fleas |
US5036072A (en) * | 1989-01-24 | 1991-07-30 | Ishihara Sangyo Kaisha Ltd. | Antiviral agent |
US5098907A (en) * | 1989-01-24 | 1992-03-24 | Ishihara Sangyo Kaisha Ltd. | Powdery pharmaceutical composition containing benzoyl urea, a dispersant and silicic acid |
US5728719A (en) * | 1991-12-23 | 1998-03-17 | Virbac, Inc. | Systemic control of parasites |
US6344476B1 (en) | 1997-05-23 | 2002-02-05 | Bayer Corporation | Inhibition of p38 kinase activity by aryl ureas |
US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
US20070020704A1 (en) * | 2003-05-20 | 2007-01-25 | Scott Wilhelm | Diaryl ureas with kinase inhibiting activity |
US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US20080009527A1 (en) * | 1997-12-22 | 2008-01-10 | Jacques Dumas | Inhibition of raf kinase using aryl and heteroaryl substituted heterocyclic ureas |
US7351834B1 (en) | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
US7528255B2 (en) | 1999-01-13 | 2009-05-05 | Bayer Pharmaceuticals Corporation | Hydroxy, ω-carboxyaryl substituted diphenyl ureas and dirivatives thereof as raf kinase inhibitors |
US7678811B2 (en) | 2002-02-11 | 2010-03-16 | Bayer Healthcare Llc | Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors |
US7838541B2 (en) | 2002-02-11 | 2010-11-23 | Bayer Healthcare, Llc | Aryl ureas with angiogenesis inhibiting activity |
US7897623B2 (en) | 1999-01-13 | 2011-03-01 | Bayer Healthcare Llc | ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors |
US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
US20110136809A1 (en) * | 2004-04-30 | 2011-06-09 | Bayer Pharmaceuticals Corporation | Substituted Pyrazolyl Urea Derivatives Useful In The Treatment Of Cancer |
US8076488B2 (en) | 2003-02-28 | 2011-12-13 | Bayer Healthcare Llc | Bicyclic urea derivatives useful in the treatment of cancer and other disorders |
US8110587B2 (en) | 2002-02-11 | 2012-02-07 | Bayer Healthcare Llc | Aryl ureas as kinase inhibitors |
US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US8637553B2 (en) | 2003-07-23 | 2014-01-28 | Bayer Healthcare Llc | Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4264605A (en) * | 1978-08-31 | 1981-04-28 | Eli Lilly And Company | 1-Benzoyl-3-(aryloxy- or arylthiopyridinyl) urea compounds |
JPS55124763A (en) * | 1979-03-19 | 1980-09-26 | Ishihara Sangyo Kaisha Ltd | 5-trifluoromethyl-2-pyridone derivative |
JPS5615272A (en) * | 1979-07-17 | 1981-02-14 | Ishihara Sangyo Kaisha Ltd | N-benzoyl-n'-phenylurea compound, its preparation, and insecticide containing the same |
JPS5731664A (en) * | 1980-07-30 | 1982-02-20 | Ishihara Sangyo Kaisha Ltd | N-benzoyl-n'-pyridyloxyphenylurea derivative |
US4366155A (en) | 1981-03-30 | 1982-12-28 | Eli Lilly And Company | 1-Benzoyl-3-(6-oxopyridazinyl)ureas, compositions, and insecticidal method |
US4511571A (en) * | 1981-10-20 | 1985-04-16 | Ciba Geigy Corporation | N-(2-Pyridyloxyphenyl)-N'-benzoyl ureas, pesticidal compositions containing same and pesticidal methods of use |
CA1233822A (en) * | 1982-12-30 | 1988-03-08 | David T. Chou | Pesticidal benzoyl ureas and process for preparation |
FR2578392B1 (en) * | 1985-03-07 | 1990-07-06 | Bayer Ag | BENZOYLIDE PRODUCTS FOR THE PROTECTION OF PLANTS AGAINST SNAILS AND SLUGS |
DE202011106852U1 (en) | 2011-10-07 | 2012-02-01 | Boge Kompressoren Otto Boge Gmbh & Co Kg | heat storage |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3748356A (en) * | 1970-05-15 | 1973-07-24 | Philips Corp | Substituted benzoyl ureas |
US4005223A (en) * | 1975-02-06 | 1977-01-25 | Bayer Aktiengesellschaft | Insecticidal 2-chloro-4'-[N-(N'-benzoyl)-ureido]-diphenyl ethers |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3962265A (en) * | 1974-01-22 | 1976-06-08 | The Dow Chemical Company | H'-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-n-methyl-n-(1-methyl-2-propynyl)urea |
DE2504982C2 (en) * | 1975-02-06 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | 4-Trifluoromethyl-4'-benzoylureido-diphenyl ether, process for their preparation and their use for combating insects |
-
1976
- 1976-10-29 JP JP51130903A patent/JPS5840946B2/en not_active Expired
-
1977
- 1977-10-21 US US05/844,174 patent/US4173638A/en not_active Expired - Lifetime
- 1977-10-25 BR BR7707099A patent/BR7707099A/en unknown
- 1977-10-27 GB GB44807/77A patent/GB1540351A/en not_active Expired
- 1977-10-28 IT IT29084/77A patent/IT1109489B/en active
- 1977-10-28 SU SU772536450A patent/SU738491A3/en active
- 1977-10-28 UA UA2536450A patent/UA6347A1/en unknown
- 1977-10-28 FR FR7732636A patent/FR2369266A1/en active Granted
- 1977-10-28 AR AR269773A patent/AR217087A1/en active
- 1977-10-29 DE DE2748636A patent/DE2748636C2/en not_active Expired
-
1981
- 1981-11-12 BE BE0/206524A patent/BE891094Q/en not_active IP Right Cessation
-
1982
- 1982-01-09 KE KE3184A patent/KE3184A/en unknown
-
1984
- 1984-12-30 MY MY75/84A patent/MY8400075A/en unknown
-
1993
- 1993-12-23 GE GEAP19931703A patent/GEP19960347B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3748356A (en) * | 1970-05-15 | 1973-07-24 | Philips Corp | Substituted benzoyl ureas |
US4005223A (en) * | 1975-02-06 | 1977-01-25 | Bayer Aktiengesellschaft | Insecticidal 2-chloro-4'-[N-(N'-benzoyl)-ureido]-diphenyl ethers |
Non-Patent Citations (1)
Title |
---|
March, J., Advanced Organic Chemistry, McGraw-Hill, New York, 1968, pp. 672-673. * |
Cited By (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4223033A (en) * | 1979-08-24 | 1980-09-16 | Zoecon Corporation | Substituted pyridine methyl esters of naphthyl acids |
US4310530A (en) * | 1979-09-07 | 1982-01-12 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N-pyridyloxy phenyl urea |
US4344951A (en) * | 1979-09-07 | 1982-08-17 | Ishihara Sangyo Kaisha Ltd. | N-Benzoyl N'-pyridyloxy phenyl urea |
US4321388A (en) * | 1979-09-11 | 1982-03-23 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N'-pyridyloxy phenyl urea |
EP0040179A2 (en) * | 1980-05-14 | 1981-11-18 | Ciba-Geigy Ag | Phenylbenzoyl urea |
EP0040179A3 (en) * | 1980-05-14 | 1982-01-20 | Ciba-Geigy Ag | Phenylbenzoyl urea |
US4418066A (en) * | 1980-05-14 | 1983-11-29 | Ciba-Geigy Corporation | Phenylbenzoylureas |
FR2492822A1 (en) * | 1980-10-24 | 1982-04-30 | Nissan Chemical Ind Ltd | HETEROCYCLIC UREA COMPOUNDS CONTAINING ETHER OR THIOETHER BINDING, PROCESS FOR THEIR PREPARATION AND INSECTICIDE COMPOSITION CONTAINING SAME |
US4425343A (en) | 1980-10-24 | 1984-01-10 | Nissan Chemical Industries, Ltd. | Benzoazine ether or thioether linkage containing urea compounds, process for producing same and insecticides containing said compounds |
US4577028A (en) * | 1981-10-20 | 1986-03-18 | Ciba-Geigy Corporation | 5-Haloalkyl-pyridines |
US4677127A (en) * | 1981-11-10 | 1987-06-30 | Ciba-Geigy Corporation | Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use |
US4897486A (en) * | 1981-11-10 | 1990-01-30 | Ciba-Geigy Corporation | 5-trifluoromethylpyridyl-2-oxy-4-fluoroanilines as intermediates |
US4431667A (en) * | 1981-12-04 | 1984-02-14 | The Upjohn Company | Imino ethers useful for controlling insect and arachnoid pests |
US4602109A (en) * | 1982-12-30 | 1986-07-22 | Union Carbide Corporation | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation |
US4659724A (en) * | 1982-12-30 | 1987-04-21 | Union Carbide Corporation | Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties |
US4540578A (en) * | 1982-12-30 | 1985-09-10 | Union Carbide Corporation | Pesticidal phenoxypyridyl benzoyl ureas |
US4973589A (en) * | 1986-08-06 | 1990-11-27 | Ciba-Geigy Corporation | Method of preventing the reinfestation of dogs and cats by fleas |
US4861799A (en) * | 1986-10-03 | 1989-08-29 | Ishihara Sangyo Kaisha Ltd. | Benzoylurea compounds and pesticides containing them |
US4985449A (en) * | 1986-10-03 | 1991-01-15 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl-N-pyridyloxy phenyl urea compounds and pesticide compositions containing them |
US5036072A (en) * | 1989-01-24 | 1991-07-30 | Ishihara Sangyo Kaisha Ltd. | Antiviral agent |
US5098907A (en) * | 1989-01-24 | 1992-03-24 | Ishihara Sangyo Kaisha Ltd. | Powdery pharmaceutical composition containing benzoyl urea, a dispersant and silicic acid |
US5728719A (en) * | 1991-12-23 | 1998-03-17 | Virbac, Inc. | Systemic control of parasites |
US6344476B1 (en) | 1997-05-23 | 2002-02-05 | Bayer Corporation | Inhibition of p38 kinase activity by aryl ureas |
US20100160371A1 (en) * | 1997-05-23 | 2010-06-24 | Gerald Ranges | Inhibition of p38 kinase activity by aryl ureas |
US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
US7625915B2 (en) | 1997-12-22 | 2009-12-01 | Bayer Healthcare Llc | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
US20080009527A1 (en) * | 1997-12-22 | 2008-01-10 | Jacques Dumas | Inhibition of raf kinase using aryl and heteroaryl substituted heterocyclic ureas |
US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
US7897623B2 (en) | 1999-01-13 | 2011-03-01 | Bayer Healthcare Llc | ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors |
US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
US7351834B1 (en) | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US7528255B2 (en) | 1999-01-13 | 2009-05-05 | Bayer Pharmaceuticals Corporation | Hydroxy, ω-carboxyaryl substituted diphenyl ureas and dirivatives thereof as raf kinase inhibitors |
US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US8841330B2 (en) | 1999-01-13 | 2014-09-23 | Bayer Healthcare Llc | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
US20100152251A1 (en) * | 2002-02-11 | 2010-06-17 | Jacques Dumas | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
US7838541B2 (en) | 2002-02-11 | 2010-11-23 | Bayer Healthcare, Llc | Aryl ureas with angiogenesis inhibiting activity |
US8071616B2 (en) | 2002-02-11 | 2011-12-06 | Bayer Healthcare Llc | Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors |
US8110587B2 (en) | 2002-02-11 | 2012-02-07 | Bayer Healthcare Llc | Aryl ureas as kinase inhibitors |
US7678811B2 (en) | 2002-02-11 | 2010-03-16 | Bayer Healthcare Llc | Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors |
US9181188B2 (en) | 2002-02-11 | 2015-11-10 | Bayer Healthcare Llc | Aryl ureas as kinase inhibitors |
US8242147B2 (en) | 2002-02-11 | 2012-08-14 | Bayer Healthcare Llc | Aryl ureas with angiogenisis inhibiting activity |
US8618141B2 (en) | 2002-02-11 | 2013-12-31 | Bayer Healthcare Llc | Aryl ureas with angiogenesis inhibiting activity |
US8076488B2 (en) | 2003-02-28 | 2011-12-13 | Bayer Healthcare Llc | Bicyclic urea derivatives useful in the treatment of cancer and other disorders |
US20070020704A1 (en) * | 2003-05-20 | 2007-01-25 | Scott Wilhelm | Diaryl ureas with kinase inhibiting activity |
US8796250B2 (en) | 2003-05-20 | 2014-08-05 | Bayer Healthcare Llc | Diaryl ureas for diseases mediated by PDGFR |
US8637553B2 (en) | 2003-07-23 | 2014-01-28 | Bayer Healthcare Llc | Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
US20110136809A1 (en) * | 2004-04-30 | 2011-06-09 | Bayer Pharmaceuticals Corporation | Substituted Pyrazolyl Urea Derivatives Useful In The Treatment Of Cancer |
US8207166B2 (en) | 2004-04-30 | 2012-06-26 | Bayer Healthcare Llc | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
Also Published As
Publication number | Publication date |
---|---|
AR217087A1 (en) | 1980-02-29 |
FR2369266B1 (en) | 1981-07-03 |
BR7707099A (en) | 1978-07-18 |
MY8400075A (en) | 1984-12-31 |
BE891094Q (en) | 1982-03-01 |
GB1540351A (en) | 1979-02-14 |
IT1109489B (en) | 1985-12-16 |
JPS5840946B2 (en) | 1983-09-08 |
KE3184A (en) | 1982-03-05 |
SU738491A3 (en) | 1980-05-30 |
DE2748636C2 (en) | 1986-07-17 |
UA6347A1 (en) | 1994-12-29 |
FR2369266A1 (en) | 1978-05-26 |
JPS5356670A (en) | 1978-05-23 |
DE2748636A1 (en) | 1978-05-03 |
GEP19960347B (en) | 1996-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4173638A (en) | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof | |
US4173637A (en) | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof | |
US4622340A (en) | Urea derivatives and pesticidal compositions containing same | |
US4344951A (en) | N-Benzoyl N'-pyridyloxy phenyl urea | |
PL112405B1 (en) | Insecticide | |
US4904696A (en) | Benzoylurea derivative and its production and use | |
EP0246061A2 (en) | A benzoylurea derivative and its production and use | |
US4150158A (en) | Oxadiazindione derivatives useful as insecticides | |
EP0167197B1 (en) | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same | |
PL139505B1 (en) | Pesticide and method of obtaining novel derivatives of benzoilurea | |
KR910004359B1 (en) | Process for the preparation of benzoylureas | |
CA1079285A (en) | N-benzoyl n'-pyridyloxy phenylurea and preparation thereof | |
GB1589259A (en) | Substituted n-benzoyl n'pyridyloxy phenyl ureas and insecticidal compositions thereof | |
EP0232080B1 (en) | Benzoylurea compounds and their production and use | |
US4783485A (en) | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same | |
CA1293516C (en) | Benzoylurea derivative and its production and use | |
AU602060B2 (en) | A benzoylurea derivative and its production and use, and aniline intermediates therefor | |
EP0278673B1 (en) | A benzoylurea derivative and its production and use | |
US5157155A (en) | Benzoylurea derivative and its production and use | |
JPS63287761A (en) | N-benzoyl-n'-trihalo-haloalkoxyphenylurea, manufacture and pesticidal use | |
KR820000407B1 (en) | Process for the preparation of substituted n-phenyl-n'-benzoyl-thioureas | |
JP2524747B2 (en) | Benzoyl urea derivatives and insecticides and acaricides containing the same as active ingredients | |
JPH02221252A (en) | Benzamide, preparation thereof and use thereof as agrochemicals | |
JPH01106855A (en) | N-benzoyl-n'-2,4-difluoro-3,5-dihalophenylureas, manufacture and use for vermicide | |
JPS63270657A (en) | Benzoylurea derivative, production thereof and insecticide containing said derivative as active ingredient |